I got a lot of requests to keep writing Paul Miller's story, so I'm going to honor those requests. Paul is going to find himself at a crossroads. He could stick with his career, a very well paid, and not unpleasant career, as a male escort/gigolo. But he finds one of his clients, Kelly, fulfills his own need for an emotional connection, something he tried to avoid in his work. Will forming a relationship with Kelly compromise his ability to have sex with the other women on a professional level? Will Kelly object to his career, since she knows what he does from the beginning? Or will he just continue his work while he is still young and handsome and in demand?
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Kelly was the daughter of Anita, my very first, and very best, client. Anita and I had an almost weekly appointment on Friday's, almost always to go to a gala of some sort or just dinner, and almost always followed by sex. She even took me with her on a vacation about two or three times a year for a week or so at a time, and she'd been my client for three years when she asked a very unusual request of me. She wanted me to have a session with Kelly, who, at 25, had never had an orgasm with a man. I agreed to meet Kelly, we connected well, and I agreed to play out her fantasy of her being a Dominatrix (for the details, see The Male Escort). Kelly had a pounding climax, and then we used a Hitachi vibrator together until we both came explosively. After that, we talked for a while and found we had a real personal connection, something I wasn't supposed to develop with any client, and something I found I was missing. It had been three years, since I started working as an escort, since I had a real personal relationship with a woman based on our mutual desires. It was very confusing for me. And now she wanted to make love with me. Heartfelt, tender, caring sex.
I should elaborate a little. The woman I worked for, Diana Royce, told me to avoid developing any real, deep connection with the women I 'escorted'. It wasn't an order, rather more of a warning, so as not to screw up my ability to do this line of work. I wasn't involved with anyone when I started and, much to my parent's chagrin, I never mentioned or introduced them to a woman as someone serious in my life during those last 3 years. I deliberately avoided getting involved with anyone, not even going on a date. And now here was a beautiful, petite woman my age (I was 28), and by talking, we were forming a connection closer than the one I had with her mother, who was in her mid 50s and whom I liked and knew very well by then. I felt that closeness after a single day, because I let myself open up to her in a way I never did with any client before.
"Well, Paul? What do you think? Do you think we could be real lovers?" Her eyes, doe-shaped, dark brown and curious, were locked on mine. The first move, if there was to be one, was up to me. "I'd like to see if we have the kind of chemistry to maybe have a personal relationship, beyond just sexual. I'm very attracted to you."
I looked back at Kelly with a distinct desire to satisfy a hunger I hadn't felt in three years. I crawled across the bed, and I ended up right in her arms, embracing and kissing. We were kissing in a way I never, ever kissed a client. This wasn't work; this was what I wanted, for me as well as for her. I couldn't even explain the way I was feeling. I barely knew this girl. It was only the second time we met and the first time we went to bed, and I felt an inner desire for her. Something personal.
We moaned as we gently rolled back and forth on the bed, from one side to the other. What remained of our clothes, mostly underwear, was gone in a few seconds as our bodies rubbed together in a very intimate manner. My fingers traced the line down her spine and her sleek nails lightly scraped me behind my neck and across my shoulders. We were sending each other direct signals. We craved each other.
"I want to taste you, Paul. I really didn't get that pleasure before. It's something I enjoy doing." Kelly said that between kisses on my lightly hairy chest.
I sighed as I said "I never would deprive you of that bliss, Kelly. Or myself, for that matter." I gave her a wink and a bit of a ball-busting grin.
"You're fun" she responded with a sexy smile that made her eyes glow. "Now, let's see if you taste as good as you look." Kelly kept kissing my tummy, teasing my Pleasure Trail, that very sensitive region from my belly button to my pubic hairline. Sensitive it was, and she blew softly on those very soft hairs. I squirmed beneath her as her hands lightly massaged my thighs, especially the inner part. Maybe she hadn't had powerful orgasms with a man before that day, but she had skills. Someone was patient with her and taught her a few things.
Kelly didn't rush things; she was teasing and fun. Her tongue moved lazily around the crown and head of my cock, then she moved down to my balls and sucked each one separately while she used her thumb on the glans. I was moaning involuntarily, and my hips kept lifting off the bed like I was trying to fuck her hand. She shifted again so she was sucking my shaft again while her fingers toyed with my balls. I tangled my fingers in her short hair (it was cut short, but it was thick and there was plenty to grab onto) and tugged a little, pulling her mouth up and down. My cock was shining from her saliva and my balls were getting wet as well. I could have cum like that, but I wanted Kelly. As my lover, and as my playmate.
I pulled my cock away from her mouth and she gave me a slight pout. "Why did you do that, Paul? I was having fun. And I would have loved to taste your cum. It's a turn on for me." Damn, she was so fucking sexy. Her eyes were shining like she had a real fire glowing inside.
"Maybe you can taste it when we finish, but I want you now. I want to make you cum from my cock, from the way I fuck you and kiss you." I moved so she was on her back and I was climbing on top of her. She showed no reluctance at all; she wanted this as well, to see if I could help her cum from more traditional sex. From making love.
Her thighs were apart for me, inviting me, and her feet were pointing to the ceiling. She grabbed my face and we kissed rapidly and with great heat as the tip of my cock met with her lower lips. We both shuddered as I eased into her pussy, slow and steady. I made sure the top of my shaft grazed along her clit so she felt every millimeter of me. Her body shook as I bottomed out, not an orgasm, but I knew from experience it was a very intense feeling for her.
"Paul, that's just wonderful!" Kelly exclaimed with her eyes wide open. "I might not need a climax if you can keep doing that to me!"
We kissed hard a couple of times as my hips moved from side to side. "Oh, no, Babe. You're going to enjoy this, every moment, just like I am. You feel great to me as well. We're both going to have such a great time."
